8 Things to do in Windsor, CA: Fill Your Days With Wine, Music, and Good Company

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Windsor is a friendly, small town located close to some of the best wine regions in the world. It’s in the Russian River Valley American Viticultural Area, with Chalk Hill, Dry Creek Valley, and Anderson Valley all close by. Yet, the town center remains more of a local’s hangout than a tourist spot, giving you an insider’s view of real life in Wine Country. And, as it turns out, the locals really do enjoy their food and wine, but, they also gather in the Town Green to celebrate holidays (Fourth of July is great) and to simply celebrate daily life with their family, friends, and neighbors. Join in on the celebration with these fun things to do in Windsor.

An Upscale Tasting Experience

Image Source: Yelp
Sonoma-Cutrer Vineyards
4401 Slusser Rd.
Windsor, CA 95492
(707) 528-1181
TripAdvisor: 4.5 stars, 32 reviews
Reservations needed

Located in the heart of the Russian River Valley, Sonoma – Cutrer Vineyards is known for its award-winning Chardonnays. It’s also an aesthetically lovely winery, with a large outdoor patio looking out over the expansive, beautifully manicured croquet field. The atmosphere is a bit more formal than most of the other area wineries, and tastings are done while sitting down at a table.

Insider tip: For a fun date, try their “Croquet and Tasting” offer. You can select three wines from their tasting menu, and then go out and play some croquet.

Wine Tasting in a Barn

Image Source: Yelp
Martinelli Winery
3360 River Rd.
Windsor, CA 95492
(707) 525-0570
TripAdvisor: 4 stars, 42 reviews
Reservations needed for specialty tasting

This family-owned winery, with a very friendly staff, is rustic housed in a charming red barn. The wines are popular, and have a sort of cult-like following among natural wine enthusiasts. The philosophy behind natural wines is to have minimal intervention during the winemaking process, so that the unique, individual taste of each harvest comes through.

Insider tip: Try the Jackass Zinfandel. The popular Zin is made from the grapes of Jackass Hill. With a 60-degree slope, it is the steepest, non-terraced hillside vineyard in Sonoma County. The family named it “Jackass Hill” because, they say, only a jackass would farm a hill that steep.

Wine Lover’s Paradise

Image Source: Yelp
Da Vine Wine Tours
Windsor, CA
(707) 318-9698
TripAdvisor: 5 stars, 54 reviews

Windsor serves as a central location to start your wine tasting adventure. And while going from one incredible winery to the next is a great way to spend the day, driving yourself from winery to winery is not always a great idea. Book a day with Da Vine Wine Tours and you won’t need to worry if you’ve had one sip too many. Denise or Dennis will drive your own car (or your rental) and let you sit back and enjoy the scenery. Tell them which regions you want to visit, or the kinds of wines you like, and they’ll tailor the tour to your interests. They know of all those tucked-away, small, family-operated wineries, and all the true, passionate winemakers who create great wines as an art form. Not only will you have a designated driver, but you’ll also get an intimate view of Wine Country.

Insider tip: They also know the best delis and picnic spots in the area, so leave them in charge of putting together a picnic lunch for you. They’ll even bring their own supplies and a cooler, so that you don’t have to think about anything besides enjoying your day.

Wine Tasting With a View

Image Source: Yelp
Russian Hill Estate Vineyards
4525 Slusser Rd.
Windsor, CA 95492
(707) 575-9428
TripAdvisor: 4 stars, 16 reviews
Reservations not needed

Russian Hill is a small, laid-back winery, with sweeping views. It’s off the mass-marketed tourism radar, and some visitors have discovered it simply because they turned on the wrong driveway to go to Sonoma – Cutrer. It’s a lucky mistake. Bring a picnic lunch, buy a bottle of wine, and stare out over the valley.

Insider tip: Take a selfie with the famed winery cat Ruska. She’s in charge of their “pest management program” and specializes in catching the larger pests such as moles, mice, and jack rabbits. Ruska is so good at her job that she’s been featured in Wine Enthusiast Magazine.

Image Source: TripAdvisor, DobleThomas.com
Windsor Town Green
Windsor, CA 95492
(707) 838-1000
TripAdvisor: 4.5 star, 7 reviews

The large Windsor Town Green is a fun, family-friendly, gathering spot with free events and holiday celebrations taking place there throughout the year. There are free concerts during the summer, and a farmers market most of the year. It is the site where locals come together to break the record for creating the world’s largest pumpkin pie (It’s also the site of the world’s longest BLT sandwich). Otherwise, it’s a common sight for residents to walk out and grab dinner down the street, or a share a few drinks at a neighborhood bar—it no wonder this place has such a community feel. It all combines for a friendly and bustling town center.

Insider tip: Make yourself at home and join in with the locals at a neighborhood pub. Patterson’s Pub & Grill makes its own, fresh Bloody Mary mix.

Go Outside and Enjoy the Natural Beauty

Image Source: Yelp
Foothill Regional Park
1351 Arata Ln.
Windsor, CA 95492
(707) 433-1625
TripAdvisor: 5 stars, 8 reviews

Go out and enjoy some of that fantastic scenic beauty that Wine Country is known for. Foothill Park is just west of downtown Windsor and is easily accessible. There are wonderful views at the top and three small lakes that can be used for fishing. It provides ample hiking trails in varying degrees of difficulty, but none of them are too strenuous or dangerous, and the park is small enough that you don’t have to worry about getting lost. Meaning, you can just drop by for a walk without having to prepare much in advance. Yet, the views and atmosphere feel like you’ve hiked all day to get out to such a natural setting.

Insider tip: You don’t need to prepare a lot, but do bring a water bottle because drinking water is only available at the parking lot trail head.


Image Source: Yelp
Windsor Golf
1340 19th Hole Dr.
Windsor, CA 95492
(707) 838-7888
TripAdvisor: 4 stars, 10 reviews

Trade in that wine glass for a golf club at the Windsor Golf Club. Formerly a stop on the PGA Nationwide Tour, this course represents Wine Country golf at it’s best. The luxurious links are surrounded by mountains and vineyards, and the 6,650-yard layout goes through a rolling landscape studded with fresh lakes, a running creek, and magnificent oaks.

Insider tip: Holes 2 and 7 were both consistently ranked among the “Top 10 Most Difficult” on the Nike Tour, so bring your A-game

Sweet Memories

Image Source: Yelp
Powell’s Sweet Shoppe
720 McClelland Dr.
Windsor, CA 95492
(707) 836-0808
TripAdvisor: 4.5, ?39 reviews

Now that you’re a grown-up, you can spend as much time as you want exploring Powell’s candy store on the Windsor Town Green, where colors explode as you walk through the door. The selection of all things sugar is amazing: There are the stacks of chocolates, bins of hard candy, and rows of see-through containers filled with gummies and jelly beans. There’s nothing quite like stumbling upon a type of candy that you haven’t tasted since you were a kid to bring back those sweet memories of youth. Powell’s specializes in finding all those hard-to-find brands: after all, it isn’t really about candy—nostalgia plays a big part in it, too.

Insider tip: Buy some sweets and head to the back of the shop to sit down in the theater seats and watch an endless loop of Willy Wonka and the Chocolate Factory.


WineCountry Collective

WineCountry is made up of a dedicated and passionate team of wine, food, and travel aficionados. We diligently explore regions, both near and far, to curate the best ideas and resources. Whether you're musing over your next wine escapade, planning a romantic weekend away, embracing the Wine Country lifestyle at home, or are simply looking to be entertained for a moment, trust us to be your comprehensive guide.